Question

Propose structures for compounds that fit the following NMR data:

(a) C₅H₁₀O

0.95$\mathrm{\delta }$(6H,double, J = 7Hz)

2.10$\mathrm{\delta }$(3H,singlet)

2.43$\mathrm{\delta }$(1H, mutiplet)

(b) C₃H₅Br

2.32$\mathrm{\delta }$(3H,singlet)

5.35 $\mathrm{\delta }$(3H,singlet)

5.45$\mathrm{\delta }$(1H, broad signet )

Short answer

Different hydrogens exhibit different chemical shift values in the ¹H NMR spectroscopy.^{Aromatic protons are deshielded and comprise a chemical shift value from 6.5 to .Alkylic protons are shielded and has a chemical shift value from 0.7 to 1.8 ppm.}

Step-by-step solution

1H NMR spectroscopy

Different hydrogens exhibit different chemical shift values in the ¹H NMR spectroscopy.^{Aromatic protons are deshielded and comprise a chemical shift value from 6.5 to .Alkylic protons are shielded and has a chemical shift value from 0.7 to 1.8 ppm.}

Step 2: Structure of the compound that fits the hydrogen NMR data

(a) The value at 0.95∂indicated as 1 in the below figure with six hydrogens corresponds to an isopropyl group. The value at indicated as two with three hydrogens corresponds to a methylketone. The value at 2.43∂indicated as three with one hydrogen correspond to an isopropyl group. The structure of the compound can be given as:

Structure of compound (a)

(b)The value at 2.32∂indicated as 1 in the figure denote the methyl group connected to the double bond. The value of 5.35∂and 5.54∂which are the other two hydrogens are the vinylic hydrogen. The structure of the compound can be given as:

Structure of compound (b)